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Jogging wearily through the streets of central Cape Town on a busy Saturday morning in November while midway through an eight-hour race is “a surreal experience,” says Eric Nathan, a landscape photographer who took up trail running about a decade ago. The small number of entrants coupled with the grueling course means that competitors are soon spaced far apart, and public awareness is minimal. “You’re engaged in a draining physical contest,” says Nathan, “but all around you, it’s business as normal.”

Every year, 150 men and women (numbers are limited as the course traverses a national park) attempt to summit Cape Town’s three iconic peaks (Devil’s Peak, Table Mountain and Lion’s Head) as quickly as possible … returning to the city center (some 1,000 feet lower than the trailhead) in between peaks! A race like this — spanning 31 miles with nearly 9,000 feet of vertical gain — should be surrounded by serious media hype, but instead the 5 a.m. start is marked not with a gunshot, but by uttering the deliberately low-key words “OK, let’s go.”

At the start of the 2017 race.

Source Courtesy of K-Way/Cape Union Mart

If this seems out of sync with modern trends, that’s because this race has a proud history to uphold. On March 7, 1897, in a self-imposed challenge, 25-year-old German immigrant Carl Wilhelm Schneeberger successfully completed the challenge in a time of 10 hours, 50 minutes — including stops for breakfast and lunch at his hotel in the center of town. At the finish, the Cape Register reports, “Mr. Schneeberger was as fresh as paint, and sat down with his pace-makers and friends to the enjoyment of a substantial meal.” His record was bettered by solo runners in 1927 and again in 1977, but the run became an annual event only in 1997, when 13 competitors gathered to celebrate the centenary of Schneeberger’s feat. The current record of 4:50:21 was set in 2012 by trail running legend AJ Calitz.

The ring of mountains surrounding Cape Town has entranced humans for millennia. The Khoi camped and hunted on the slopes of Hoerikwaggo (“the mountain in the sea”), while Portuguese sailor Antonio de Saldanha made the first recorded ascent of Table Mountain in 1503. And Scottish noblewoman Lady Anne Barnard became the “first white woman” to the top in 1797. Since 1929, a cable car has offered an easy way out, but the trio of mountains remains an unlikely adventurer’s playground, surrounded by a city of 4 million souls.

By the time you tackle Lion’s Head, supposedly the easiest of the three peaks, “you’re totally buggered.”

As a lifelong resident of the city, I have hiked each of the three peaks a few times, but the thought of tackling them all in a single day (and returning to the city center between climbs) fills me with dread. In what sounds like a challenge, Nathan tells me that “the hardest part is deciding to give it a bash,” but he also admits that not all of the obstacles are mental. The predawn start near some of the city’s busiest pubs and clubs “can be interesting,” he adds. (Last year, the official start was moved, and the first part of the route was changed to avoid the Long Street revelers). Once on the course, the path on the upper sections of Devil’s Peak has loads of confusing shortcuts. The 2,300-foot rock staircase up Platteklip Gorge to the summit of Table Mountain is the route’s most physically demanding section, and the endless stream of unaware day-hikers can also be frustrating. And by the time you tackle Lion’s Head, supposedly the easiest of the three peaks, “you’re totally buggered,” he laughs.

But, says Nathan, the sense of achievement and the ceramic trophy, which depicts the three peaks, more than justify the sacrifice. Artist and runner Don Hartley, who organized (and won) the 1997 centenary run makes every single trophy by hand and even donates some of his paintings as prizes for the winners and anyone who’s completing their 10th race.

“It’s becoming increasingly difficult to remain under the radar,” says co-organizer Gavin Snell, who has completed all 21 iterations of the modern race. “But that’s the way we like it.”

* Correction: The original version of this story misstated the extent of vertical gain covered in the race.

Do It: The Three Peaks Challenge

The old-fashioned way: The 2018 edition takes place on Nov. 3. However entry submission are limted to 150, so you may have to wait a year or two to be accepted.

In the dark: The Bat Run follows a similar route at night. It takes place in late February or early March (as close to a full moon as possible), but the 2018 edition has already sold out.

DIY: Not gonna make either event? The Three Peaks can be climbed 365 days a year, but only serious trail runners with local knowledge should attempt the route.